159 Cross Hwy

Redding, CT 06896

$629,000
Price
3
Beds
1,671 Sq. Ft.
$376 / Sq. Ft.
1,671
Sq. Ft.
$376
per Sq. Ft.
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Under Contract - Continue To Show
Under Contract - Continue To Show

Description

Charming turn-of-the-century Craftsman farmhouse on one of Redding's most picturesque Scenic Roads - a rare find for those seeking space, character, and a genuine sense of place within reach of the city, but worlds away from it. Featuring authentic period details including crown molding, a bay window, beautiful hardwood floors, and soaring 9-foot ceilings, this three-bedroom, two-bath home balances historic charm with thoughtful modern updates. A newly expanded primary suite and a brand-new full...Charming turn-of-the-century Craftsman farmhouse on one of Redding's most picturesque Scenic Roads - a rare find for those seeking space, character, and a genuine sense of place within reach of the city, but worlds away from it. Featuring authentic period details including crown molding, a bay window, beautiful hardwood floors, and soaring 9-foot ceilings, this three-bedroom, two-bath home balances historic charm with thoughtful modern updates. A newly expanded primary suite and a brand-new full bath on the second floor - complete with new HVAC - make the home as comfortable as it is characterful. Once the original switchboard for Redding Ridge, the property sits on a large, level lot with mature landscaping, spectacular perennial gardens that bloom spring through fall, a deck, brick terrace, and storage shed. The new roof and all-new windows mean the big work is done - just move in. Beyond the property itself, Redding delivers the lifestyle that's increasingly hard to find closer to the city: miles of open space, hiking trails, and beloved local institutions like the Mark Twain Library, New Pond Farm, Huntington State Park, and Putnam Park. It's a town with a strong sense of community, where weekends mean farmers markets and trail walks, not traffic. Additional highlights include an EV charger, generator, and 25 years of careful stewardship. History, updates, and room to grow - all in one of Connecticut's most desired small towns
  1. Listed by Bill Whitehead • Berkshire Hathaway NE Prop.
    P: (203)-606-8536 C: (203)-606-8536 williamwhitehead@bhhsne.com
  2. Listed by John Talley • Berkshire Hathaway NE Prop.
    P: (203)-438-9501 C: (203)-947-1057 johntalley@bhhsne.com

Property Details for 159 Cross Highway

Basement Description
Partial, Unfinished
Direct Waterfront
No
Expected Active Date
05-22-2026
Neighborhood
Redding Ridge
Style
Antique, Farm House
Garage Parking Info
Driveway, Unpaved
Swimming Pool
No
Expected On Market Date
05-22-2026
LISTING UPDATED: 05/28/2026 11:30 PM

Property Details for 159 Cross Highway

StatusUnder Contract - Continue To Show
MLS #24165406
Days on Market6
Taxes$8,487 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1900
Lot Size0.86 AC / 37,461 SF
CountyFairfield County
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Location

Listing Courtesy of Berkshire Hathaway NE Prop., Bill Whitehead; Berkshire Hathaway NE Prop., John Talley
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Building Information for 159 Cross Highway

Stories-Year Built1900Building Size-Lot Size0.86 AC / 37,461 SF

Payment Calculator

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$3,842 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,134

Property Taxes

$707

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 159 Cross Highway

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly - Corner of Cross Highway & Newtown Turnpike.
  • Elementary School: Redding
  • High School: Joel Barlow
  • Latitude: 41.312506
  • Longitude: -73.356069
  • Middle Jr High School: John Read
  • Neighborhood Amenities: Golf Course, Lake, Library, Park, Stables/Riding, Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 6
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $8,487
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Porch, Deck, Gutters
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Dishwasher, Washer, Electric Dryer
  • Attic Description: Unfinished, Access Via Hatch
  • Cooling System: Central Air, Window Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Interior Features: Cable - Available, Security System
  • Laundry Room Info: Lower Level
  • Laundry Room Location: Basement
  • Rooms Total: 7
Room 1
  • Room Entry Order: 1
  • Room Features: Bay/Bow Window,9 ft+ Ceilings,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Bay/Bow Window,9 ft+ Ceilings,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Skylight,Cathedral Ceiling,Double-Sink,Eating Space,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 4
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Level: Main
  • Room Type: Den
Room 5
  • Listing Key: 4EE52DF794D29D12E063E201100ABA78
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Whirlpool Tub,Tub w/Shower,Tile Floor
  • Room Level: Main
  • Room Type: Full Bath
Room 6
  • Room Entry Order: 6
  • Room Features: Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: Skylight,Vaulted Ceiling,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Features: Vaulted Ceiling,Wall/Wall Carpet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 9
  • Listing Key: 4EE52DF794D29D12E063E201100ABA78
  • Room Entry Order: 9
  • Room Features: Stall Shower,Tile Floor
  • Room Level: Upper
  • Room Type: Full Bath
Property
Property and Assessments
  • Color: Sage Green/Gray
  • Construction Description: Frame
  • Driveway Type: Private, Unpaved, Gravel
  • Exterior Siding: Clapboard
  • Foundation Type: Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Shingle
  • Year Built: 1900
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Description: Town has updated square footage to 1671 with the recent primary bedroom expansion.
  • Living Area SQFT Per Public Records: 1467
Lot Information
  • Lot Description: Corner Lot, Lightly Wooded, Level Lot, Cleared
  • Parcel Number: 268864
  • Sq Ft Est Heated Above Grade: 1671.0
  • Sq Ft Total: 1671.0
  • Zoning: R-2
Utilities
  • Energy Features: Generator, Generator Ready
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 159 Cross Highway

DateEvent & SourcePriceAppreciation
Dec 13, 2000

Closed (Public Record)

Public Record #91142103

$350,000

+13.2% / yr

Jan 29, 1998

Closed (Public Record)

Public Record #91142953

$245,000—
DateEvent & SourcePrice
12/13/2000

Closed (Public Record)

Public Record #91142103

$350,000

+13.2% / yr

01/29/1998

Closed (Public Record)

Public Record #91142953

$245,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 159 Cross Highway

Taxable ValueLand$140,300Additions$147,000Total$287,300
Tax Record2024$8,487 ($707 / month)
Home Facts
Beds3Baths1Total Finished SqFt1,467 SqFtAbove Grade Finished SqFt1,467 SqFtStories2Lot Size37,462 SqFtStyleSingle Family ResidenceYear Built1900Year Renovated1981ZoningR-2CountyWESTERN CONNECTICUTAPNREDD M:23 L:167

Schools near 159 Cross Highway

This home is within Redding School District.
Rating
School
Type
Grades
Distance
Redding Elementary School
Public - PK to 4
John Read Middle School
Public - 5 to 8
Joel Barlow High School
Public - 9 to 12
Rating
School
Distance
Redding Elementary School
PublicPK to 4

John Read Middle School
Public5 to 8

Joel Barlow High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of Berkshire Hathaway NE Prop., Bill Whitehead; Berkshire Hathaway NE Prop., John Talley

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.